The present invention relates to phenylethyl methylcarbonate having the structure: ##STR2## processes for preparing same and for preparing mixtures of same by reacting phenyl ethyl acetate with dimethyl carbonate in the presence of an alkalide metal alkoxide catalyst, and mixtures of phenylethyl methylcarbonate with other perfumery materials such as 3-methyl-1-phenyl-pentanol-5 and/or one or more butanoyl cyclohexane derivatives defined according to the following structures: ##STR3## (generic structure) wherein one of the dashed lines is a carbon-carbon double bond or two of the dashed lines is a carbon-carbon double bond but that when the two of the dashed lines represents a carbon-carbon double bond the carbon-carbon double bonds are conjugated. ##STR4## (wherein the dashed line represents a configuration of the butenoyl moiety "trans" with respect to the methyl moiety at the "two" position on the cyclohexene ring). ##STR5##
Materials which can provide natural rose nuances and which provide aroma profiles described as "rose, hyacinth, sweet powdery with fresh flower petal-like, fresh fruit and pineapple-like undertones" are highly desired in the art of perfumery. Provision of the "fresh petal-like" nuance is novel in the art of perfumery. Many of the natural substances which are alleged to provide rose fragrances and contributes certain of the desired nuances to perfumery compositions are high in cost, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
The prior art contains a large number of teachings regarding the use of organic carbonates in augmenting or enhancing the aroma of perfumes.
Thus, U.S. Pat. No. 4,033,993 discloses the use of organic carbonates defined according to the structure: ##STR6## wherein R.sub.1 is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms, alkenyl having from 2 to 5 carbon atoms and alkynyl having from 2 to 5 carbon atoms. U.S. Pat. No. 4,033,993 describes, for example, methyl-1-ethynycyclohexyl carbonate having a fruity, herbal and complex odor and distinct fragrance of dill. In addition, U.S. Pat. No. 4,033,993 describes methyl cyclooctyl carbonate as having an herbal, natural and complex fragrance which is distinguished by a strong and long clinging flowery jasmine scent and further indicates its use in jasmine perfume compositions. U.S. Pat. No. 4,033,993 describes the preparation of the compounds defined according to the structure: ##STR7## according to the reaction: ##STR8## wherein R.sub.1 and R.sub.2 are defined as above.
In addition, U.S. Pat. No. 4,080,309 describes the perfume use of the carbonates defined according to the structure: ##STR9## wherein R.sub.1 ' is a moiety having from 8 to 12 carbon atoms selected from the group consisting of alkylcyclohexyl, alkenylcyclohexyl, alkynylcyclohexyl and cycloalkyl and R.sub.2 ' is a moiety selected from the group consisting of alkyl having from 1 to 5 carbon atoms. Described in U.S. Pat. No. 4,080,309 are also such compounds as methyl cyclooctyl carbonate and the use thereof in jasmine perfume formulations. As is the case in U.S. Pat. No. 4,033,993, the carbonates of 4,080,309 are indicated to be prepared according to the reaction: ##STR10##
Arctander "Perfume & Flavor Chemicals (Aroma Chemicals)" published in 1969, at Volume 2, Monograph No. 2528 describes the chemical phenylethyl ethylcarbonate defined according to the structure: ##STR11## "as pleasant etheral-alcohol-like, sweet and rather powerful odor of poor tenacity . . . The title material finds some use in perfume compositions as part of topnote compositions, floral bases and certain types of herbaceous fragrance. It blends well with Lavender and Clary Sage, and it has a mellowing effect upon the alifatic aldehydes and aldehydic topnote bases, etc.
The ester is also interesting by its effect of "lifting" a musk odor so that the must becomes perceptible at a much earlier state of the perfume evaporation. In a way, the opposite of a fixative effect, but quite attractive when used with the proper amount and type of musk. PA1 Produced from Ethyl monochloroformate and Phenylethylalcohol in Chloroform with Pyridine as a catalyst."
In addition, U.S. Pat. No. 4,217,253 issued on Aug. 12, 1980, discloses processes and compositions for use in perfume aroma augmenting, modifying, altering and enhancing compositions and as perfume, cologne and perfumed article aroma imparting materials of mixtures of 3-methyl-1-phenyl-pentanol-5- and one or more butanoyl cyclohexane derivatives defined according to the following structures: ##STR12## (generic structure) wherein one of the dashed lines is a carbon-carbon double bond or two of the dashed lines is a carbon-carbon double bond but that when the two of the dashed lines represents a carbon-carbon double bond the carbon-carbon double bonds are conjugated. ##STR13## (wherein the dashed line represents a configuration of the butenoyl moiety "trans" with respect to the methyl moiety at the "two" position on the cyclohexene ring). ##STR14##
In addition, U.S. Pat. No. 4,028,279 entitled "Novel Fragrance Compositions Containing 2,6,6-Trimethyl-1-Cyclohexene-1-yl Acetaldehyde and Phenyl C.sub.6 Ketone" relates to mixtures of (i) either or both of the phenyl C.sub.6 ketones, 2,5-dimethyl-5-phenylhexanone-4 and 2,5-dimethyl-5-phenylhexen-1-one-3 and (ii) 2,2,6-trimethyl-cyclohexen-1-yl acetaldehyde used to alter, modify, enhance or impart aromas in or to perfumes, perfume compositions and/or perfumed articles. It is disclosed in said U.S. Pat. No. 4,028,279 that such perfume compositions containing such mixtures have intense rosey aromas with woody, green and earthy notes. The structure of the phenyl C.sub.6 ketones disclosed in U.S. Pat. No. 4,208,279 is: ##STR15## the structure of the betacyclohomocitral used in U.S. Pat. No. 4,028,279 is: ##STR16## wherein the dashed line may be either a carbon-carbon single bond or a carbon-carbon double bond.
In U.S. Pat. No. 3,959,508, issued on May 25, 1976 mixtures of (i) 2,2,6-trimethyl-1-cyclohexen-1-yl acetaldehyde and (ii) 2,6,6-trimethyl crotonyl-1,3-cyclohexadiene having the structure: ##STR17## are indicated to produce in perfumes, rosey, woody, camphoraceous, green and earthy notes.
Nothing in the prior art including U.S. Pat. No. 3,959,508, 4,028,279, 4,217,253 or the Arctander reference implies or states that phenylethyl methylcarbonate or such mixtures as are disclosed and claimed in the instant case can be used to enhance and extend specific aroma nuances particularly in the rose and fresh petal aroma classification.